GB408451A - Manufacture of alkyl-mercury-mercapto compounds - Google Patents
Manufacture of alkyl-mercury-mercapto compoundsInfo
- Publication number
- GB408451A GB408451A GB11109/33A GB1110933A GB408451A GB 408451 A GB408451 A GB 408451A GB 11109/33 A GB11109/33 A GB 11109/33A GB 1110933 A GB1110933 A GB 1110933A GB 408451 A GB408451 A GB 408451A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- carboxylic acid
- mercaptobenzoxazole
- carboxylic
- mercaptobenzthiazole
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 alkali metal salts Chemical class 0.000 abstract 6
- 239000005711 Benzoic acid Substances 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract 3
- BUSBFZWLPXDYIC-UHFFFAOYSA-N arsonic acid Chemical group O[AsH](O)=O BUSBFZWLPXDYIC-UHFFFAOYSA-N 0.000 abstract 3
- 229940100892 mercury compound Drugs 0.000 abstract 3
- FLFWJIBUZQARMD-UHFFFAOYSA-N 2-mercapto-1,3-benzoxazole Chemical compound C1=CC=C2OC(S)=NC2=C1 FLFWJIBUZQARMD-UHFFFAOYSA-N 0.000 abstract 2
- LLOAINVMNYBDNR-UHFFFAOYSA-N 2-sulfanylidene-1,3-dihydrobenzimidazole-5-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2NC(=S)NC2=C1 LLOAINVMNYBDNR-UHFFFAOYSA-N 0.000 abstract 2
- NLPZRWDNWKLLCI-UHFFFAOYSA-N 2-sulfanylidene-3h-1,3-benzothiazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2SC(=S)NC2=C1 NLPZRWDNWKLLCI-UHFFFAOYSA-N 0.000 abstract 2
- GUGDWCNTMFYFRB-UHFFFAOYSA-N 2-sulfanylidene-3h-1,3-benzoxazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2OC(=S)NC2=C1 GUGDWCNTMFYFRB-UHFFFAOYSA-N 0.000 abstract 2
- 150000001735 carboxylic acids Chemical class 0.000 abstract 2
- NZMAJUHVSZBJHL-UHFFFAOYSA-N n,n-dibutylformamide Chemical compound CCCCN(C=O)CCCC NZMAJUHVSZBJHL-UHFFFAOYSA-N 0.000 abstract 2
- 239000012991 xanthate Substances 0.000 abstract 2
- OICZZBOSFSIWOC-UHFFFAOYSA-N (2-sulfanylidene-1,3-dihydrobenzimidazol-5-yl)arsonic acid Chemical compound SC=1NC2=C(N1)C=CC(=C2)[As](O)(=O)O OICZZBOSFSIWOC-UHFFFAOYSA-N 0.000 abstract 1
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical class C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 abstract 1
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 abstract 1
- QKZCJCIRGUQTJA-UHFFFAOYSA-N 2-sulfanylidene-3h-1,3-benzothiazole-7-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1SC(S)=N2 QKZCJCIRGUQTJA-UHFFFAOYSA-N 0.000 abstract 1
- QNPUJYUTYBZIRT-UHFFFAOYSA-N 2-sulfanylidene-3h-1,3-benzoxazole-4-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1N=C(S)O2 QNPUJYUTYBZIRT-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000002421 anti-septic effect Effects 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- QSGMYNMNVDYQRX-UHFFFAOYSA-N ethylmercury 2-sulfanylidene-3H-1,3-benzothiazole-5-carboxylic acid Chemical compound SC=1SC2=C(N1)C=C(C=C2)C(=O)O.CC[Hg] QSGMYNMNVDYQRX-UHFFFAOYSA-N 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 abstract 1
- 229910052753 mercury Inorganic materials 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 229920001021 polysulfide Polymers 0.000 abstract 1
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/10—Mercury compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Organo-mercury compounds are prepared by treating an alkyl-mercury compound with a mercaptobenzoxazole or mercaptobenzimidazole containing an acid group, the mercapto group being in the heterocyclic ring. Acid groups are, for instance, the carboxylic, sulphonic or arsonic acid group. Among the alkyl groups attached to mercury are mentioned methyl, ethyl, propyl, butyl, amyl and isoamyl. The products possess antiseptic properties; they may be converted into their alkali metal salts which are soluble in water. Examples are given of the interaction of (1) ethylmercuric chloride with 2-mercaptobenzoxazole-5-carboxylic acid, 2 - mercaptobenzoxazole - 4 - carboxylic acid, 2 - mercaptobenzimidazole - 6 - sulphonic acid and 2 - mercaptobenzimidazole - 5 - arsonic acid (see German Specification 531,801); (2) n-propyl-mercuric chloride with 2-mercaptobenzoxazole-5-carboxylic acid. The formul of the products are given. Specification 329,987, [Class 2 (iii)], is referred to. 2 - Mercaptobenzoxazole - 4 or 5 - carboxylic acid is prepared by reacting 2-amino-3-hydroxy-1-benzoic acid or 3-amino-4-hydroxy-1-benzoic acid with an alkali metal xanthate. 2 - Mercaptobenzimidazole - 6 - sulphonic acid is obtained by treating 1 : 2-diaminobenzene-4-sulphonic acid with an alkali metal xanthate. The Specification as open to inspection under Sect. 91 describes also the use of cycloalkyl-mercury compounds and the treatment of mercaptobenzthiazoles containing an acid group. Cycloalkyl groups specified are cyclohexyl and methylcyclohexyl. According to an example, 2 - mercaptobenzthiazole - 5 - carboxylic acid is treated with ethylmercuric chloride and the resulting 2-ethylmercury-mercaptobenzthiazole-5-carboxylic acid converted into its sodium salt. From 2-mercaptobenzthiazole-7-carboxylic acid the 2-cyclohexylmercury compound is obtained with the aid of cyclohexylmercuric chloride. 2 - Mercaptobenzthiazole - 5 - carboxylic and arsonic acids. The carboxylic acid is prepared by converting 3-nitro-4-chloro-1-benzoic acid into the 4-mercapto compound using sodium polysulphide and reacting the mercapto compound with potassium xanthate. In German Specification 519,987 is described the preparation of the corresponding arsonic acid by the same process. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE408451X | 1932-04-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB408451A true GB408451A (en) | 1934-04-12 |
Family
ID=6422296
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB11109/33A Expired GB408451A (en) | 1932-04-16 | 1933-04-13 | Manufacture of alkyl-mercury-mercapto compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB408451A (en) |
-
1933
- 1933-04-13 GB GB11109/33A patent/GB408451A/en not_active Expired
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